Record Information
Creation date2011-09-21 00:15:29 UTC
Update date2015-07-21 06:57:15 UTC
Primary IDFDB022533
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDiadenosine hexaphosphate
DescriptionDiadenosine hexaphosphate (AP6A) is a diadenosine polyphosphate. Diadenosine polyphosphates (APnAs, n = 3-6) are a family of endogenous vasoactive purine dinucleotides which have been isolated from thrombocytes. APnAs have been demonstrated to be involved in the control of vascular tone as well as the growth of vascular smooth muscle cells and hence, possibly, in atherogenesis. APnAs isolated substances are AP3A, AP4A, AP5A, and AP6A. APnAs are naturally occurring substances that facilitate tear secretion; they are released from the corneal epithelium, they stimulate tear production and therefore they may be considered as physiological modulators of tear secretion. The APnAs were discovered in the mid-sixties in the course of studies on aminoacyl-tRNA synthetases (aaRS). APnAs have emerged as intracellular and extracellular signalling molecules implicated in the maintenance and regulation of vital cellular functions and become considered as second messengers. Great variety of physiological and pathological effects in mammalian cells was found to be associated with alterations of APnAs. APnAs are polyphosphated nucleotidic substances which are found in the CNS and are known to be released in a calcium-dependent manner from storage vesicles in brain synaptosomes. AP6A is an avid inhibitor of eosinophil-derived neurotoxin (EDN). EDN is a catalytically proficient member of the pancreatic ribonuclease superfamily secreted along with other eosinophil granule proteins during innate host defense responses and various eosinophil-related inflammatory and allergic diseases. The ribonucleolytic activity of EDN is central to its antiviral and neurotoxic activities and possibly to other facets of its biological activity. AP6A have been demonstrated to be involved in the control of vascular tone as well as the growth of vascular smooth muscle cells and hence, possibly, in atherogenesis. AP6A have been identified in human platelets and shown to be an important modulator of cardiovascular function. (PMID: 11212966, 12738682, 11810214, 9607303, 8922753, 16401072, 12738682, 10094777) [HMDB]
CAS Number56983-23-4
Adenosine 5'-hexaphosphate 5'-ester with adenosineChEBI
Diadenosine 5',5''''-P1,P6-hexaphosphateChEBI
Adenosine 5'-hexaphosphoric acid 5'-ester with adenosineGenerator
Diadenosine 5',5''''-P1,P6-hexaphosphoric acidGenerator
P1,P6-Di(adenosine-5')hexaphosphoric acidGenerator
Diadenosine hexaphosphoric acidGenerator
Adenosine 5'-(heptahydrogen hexaphosphate) p->5'-ester with adenosineHMDB
Adenosine 5'-(heptahydrogen hexaphosphate)5'-5'-ester with adenosineHMDB
P1,P6-Bis(5'-adenosyl)hexaphosphoric acidHMDB
p(1),p(6)-Bis(5'-adenosyl)hexaphosphoric acidHMDB
Diadenosine hexaphosphateChEBI
Adenosine 5'-(heptahydrogen hexaate) P->5'-ester with adenosineHMDB
Adenosine 5'-(heptahydrogen hexaate)5'-5'-ester with adenosineHMDB
Adenosine 5'-(heptahydrogen hexaphosphate) P->5'-ester with adenosinehmdb
Adenosine 5'-hexaate 5'-ester with adenosineChEBI
Adenosine 5'-hexaic acid 5'-ester with adenosineGenerator
Diadenosine 5',5''''-P1,P6-hexaateChEBI
Diadenosine 5',5''''-P1,P6-hexaic acidGenerator
Diadenosine hexaateChEBI
Diadenosine hexaic acidGenerator
P1,P6-Di(adenosine-5')hexaic acidGenerator
Predicted Properties
Water Solubility6.99 g/LALOGPS
pKa (Strongest Acidic)0.28ChemAxon
pKa (Strongest Basic)5.3ChemAxon
Physiological Charge-6ChemAxon
Hydrogen Acceptor Count26ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area527.03 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity187.85 m³·mol⁻¹ChemAxon
Polarizability76.38 ųChemAxon
Number of Rings6ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H30N10O25P6
IUPAC name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid
InChI IdentifierInChI=1S/C20H30N10O25P6/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(49-19)1-47-56(35,36)51-58(39,40)53-60(43,44)55-61(45,46)54-59(41,42)52-57(37,38)48-2-8-12(32)14(34)20(50-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H,45,46)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1
Isomeric SMILESNC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)N4C=NC5=C(N)N=CN=C45)[C@@H](O)[C@H]3O)C2=NC=N1
Average Molecular Weight996.3468
Monoisotopic Molecular Weight995.980925632
Description Belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
Sub ClassNot Available
Direct Parent(5'->5')-dinucleotides
Alternative Parents
  • (5'->5')-dinucleotide
  • Purine ribonucleoside polyphosphate
  • Purine nucleotide sugar
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Alkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Phosphoric acid ester
  • Imidolactam
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Secondary alcohol
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Amine
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physiological effect

Health effect:


Biological location:


Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
EI-MS/GC-MSNot Available
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0910110002-59d115c90a4481a6b0072015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-d3bcef479d59e691d5b82015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0900000000-8dec47b8f02e8a6ac5a72015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-0700000209-de23da8b809775f36d572015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000200-eec87d1063e1b19d703a2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-1902401000-c06f9d4097503496c4b32015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000009-1da203db6bf6303096a02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0100001329-9afe5ff0f93ff13bf2a82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000b-0103149204-ccb4974c1451a6de78f32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0100000009-e59c713225edd8e0460d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0300000039-0a05007bbbf9147ab5f02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0900000110-66251e85696bf2211dd42021-09-22View Spectrum
NMRNot Available
ChemSpider ID110267
ChEMBL IDNot Available
KEGG Compound IDC20190
Pubchem Compound ID123694
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
MSDSNot Available
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference